Thiolative Annulation of <i>N</i>-Benzyl-<i>N</i>-cyanopropiolamides Leading to Divergent Synthesis of Pyrroloquinazolin-1-ones and Maleimides
An unprecedented successive radical-promoted thiolative annulation/Pd-catalyzed C-H amination of <i>N</i>-benzyl-<i>N</i>-cyanopropiolamides to access pyrrolo[2,1-<i>b</i>]quinazolin-1(9<i>H</i>)-ones in a one-pot manner is described. Moreover, altering the amination step with oxidation (reagent switch) offered maleimides from the same set of readily accessible precursors. Both transformations display versatility across a wide range of substrates, enabling the efficient access to various functionalized quinazolin-1-ones and maleimides in good yields.
Authors
- Nagender Punna (ORCID: https://orcid.org/0000-0003-2761-6078)
- Chada Raji Reddy (ORCID: https://orcid.org/0000-0003-1491-7381)
- Uprety Ajaykumar
- Luc Neuville (ORCID: https://orcid.org/0000-0002-4648-2469)
- Géraldine Masson (ORCID: https://orcid.org/0000-0003-2333-7047)
- Anootha Neeliveettil
Institutions
- Centre National de la Recherche Scientifique (FR)
- Institut de Chimie des Substances Naturelles (FR)
- Université Paris-Saclay (FR)
- Indian Institute of Chemical Technology (IN)
- Academy of Scientific and Innovative Research (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-05-08
- DOI
- https://doi.org/10.1021/acs.orglett.5c01553
- Citations
- 5
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 4.68
Funders
- Department of Science and Technology, Ministry of Science and Technology, India
- Indo-French Centre for the Promotion of Advanced Research